Sodium Hydroxide → HCID 11663420, compound

HRID 751599Notes

Reaction equation

HRID 751599 reaction equation
C([O:3][C:4](=[O:40])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[N:14]([CH:37]=[CH:38][N:39]=3)[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25](=[O:36])[C:26]4[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=4)[CH:19]=3)[N:17]=2)=[CH:7][CH:6]=1)C.[OH-].[Na+]>C(O)C>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([C:25]([NH:24][C:20]2[CH:19]=[C:18]([C:16]3[N:17]=[C:12]([NH:11][C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:40])=[O:3])=[CH:6][CH:7]=4)[C:13]4[N:14]([CH:37]=[CH:38][N:39]=4)[CH:15]=3)[CH:23]=[CH:22][CH:21]=2)=[O:36])=[CH:31][CH:30]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59754693HCID 59754693, compound

Product 1

HCID 11663420HCID 11663420, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-{6-[3-(4-tert-butyl-benzoylamino)phenyl]imidazo[1,2-a]pyrazin-8-ylamino}benzoic acid ethyl ester (20) (30 mmol), 1N aqueous sodium hydroxide (50 mL), and ethanol (80 mL) is heated at reflux for 1.5 hrs. The mixture is cooled and the ethanol removed in vacuo. The residue is diluted with 1N sodium hydroxide (30 mL) and washed with ethyl acetate (2×100 mL). The aqueous layer is brought to pH 6 with 3 N HCl, and the mixture is filtered to give 4-{6-[3-(4-tert-butyl-benzoylamino)phenyl]imidazo[1,2-a]pyrazin-8-ylamino}benzoic acid (21) as a cream solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.5 hrs
  3. temperatureThe mixture is cooled
  4. customthe ethanol removed in vacuo
  5. additionThe residue is diluted with 1N sodium hydroxide (30 mL)
  6. washwashed with ethyl acetate (2×100 mL)
  7. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-2ba877726b53475c94ffa0a37d9240bf
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

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